Biosynthesis of isoprenoids in Escherichia coli: The fate of the 3-H and 4-H atoms of 1-deoxy-D-xylulose

(Note: The full text of this document is currently only available in the PDF Version )

José-Luis Giner, José-Luis Giner, Bernhard Jaun and Duilio Arigoni


Abstract

The ubiquinone obtained from E. coli after feeding of 1-deoxy[3-2H]xylulose shows labeling of the E-methyl group in the terminal unit and of all other positions derived from the terminal methylene group of isopentenyl pyrophosphate, whilst label from 1-deoxy[4-2H]xylulose is retained exclusively in the double bond corresponding to the dimethylallyl pyrophosphate starter unit.


References

  1. M. Rohmer, M. Knani, P. Simonin, B. Sutter and H. Sahm, Biochem. J., 1993, 295, 517 CAS.
  2. S. T. J. Broers, ETH Thesis ( 1994) No. 10978, Zürich.
  3. J. Schwender, M. Seemann, H. K. Lichtenthaler and M. Rohmer, Biochem. J., 1996, 316, 73 CAS.
  4. A. Cartayrade, M. Schwarz, B. Jaun and D. Arigoni, Second Symposium of the European Network on Plant Terpenoids, Strasbourg Bischenberg, France, Jan. 23–27, 1994, Abstr. P1 Search PubMed; M. K. Schwarz, ETH Thesis ( 1994) No. 10951, Zürich; W. Eisenreich, B. Menhard, P. J. Hylands, M. H. Zenk and A. Bacher, Proc. Natl. Acad. Sci. U.S.A., 1996, 93, 6431 Search PubMed; W. Eisenreich, S. Sagner, M. H. Zenk and A. Bacher, Tetrahedron Lett., 1997, 38, 3889 Search PubMed; H. K. Lichtenthaler, J. Schwender, A. Disch and M. Rohmer, FEBS Lett., 1997, 400, 271 CrossRef CAS; W. Knoss, B. Reuter and J. Zapp, Biochem. J., 1997, 326, 449 CrossRef CAS.
  5. D. Arigoni, S. Sagner, C. Latzel, W. Eisenreich, A. Bacher and M. H. Zenk, Proc. Natl. Acad. Sci. U.S.A., 1997, 94, 10 600 CrossRef CAS; J. G. Zeidler, H. K. Lichtenthaler, H. U. May and F. W. Lichtenthaler, Z. Naturforsch., Teil C, 1997, 52, 15 Search PubMed; J. Schwender, J. Zeidler, R. Groener, C. Mueller, M. Focke, S. Braun, F. W. Lichtenthaler and H. K. Lichtenthaler, FEBS Lett., 1997, 414, 129 CrossRef CAS; S. Sagner, C. Latzel, W. Eisenreich, A. Bacher and M. H. Zenk, Chem. Commun, 1998, 221 RSC.
  6. T. Duvold, J.-M. Bravo, C. Pale-Grosdemange and M. Rohmer, Tetrahedron Lett., 1997, 38, 4769 CrossRef CAS.
  7. S. Sagner, W. Eisenreich, M. Fellermeier, C. Latzel, A. Bacher and M. H. Zenk, Tetrahedron Lett., 1998, 39, 2091 CrossRef CAS.
  8. J.-L. Giner, Tetrahedron Lett., 1998, 39, 2479 CrossRef CAS.
  9. D. Zhou and R. H. White, Biochem. J., 1991, 273, 627 CAS.
  10. S. Terao, K. Kato, M. Shiraishi and H. Morimoto, J. Chem. Soc., Perkin Trans. 1, 1978, 1101 RSC; Y. Naruta, J. Org. Chem., 1980, 45, 4097 CrossRef CAS These assignments were independently confirmed by HMBC and HMQC NMR experiments.
  11. For a review, see C. D. Poulter and H. C. Rilling, in Biosynthesis of Isoprenoid Compounds, ed. J. W. Porter and S. L. Spurgeon, Wiley, New York, 1981, vol. 1, p. 161 Search PubMed.
  12. S. Fujisaki, T. Nishino and H. Katsuki, J. Biochem., 1986, 99, 1327 CAS.
  13. D. Arigoni, D. E. Cane, J. H. Shim, R. Croteau and K. Wagschal, Phytochemistry, 1993, 32, 623 CrossRef CAS and references cited therein.
Click here to see how this site uses Cookies. View our privacy policy here.